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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$905
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$5-$570
Fishing Charters
Let a captain do the driving while you do the fishing
$5-$195
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$800
Sailboats
Set sail with these traditional wind-powered boats
$120-$370
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$395
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$5-$150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
Ozer
2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
Had the most spectacular afternoon aboard Monika's yacht for a friend's birthday party. The space comfortably fits 12 people, with belongings, food and drinks. The sound system is awesome and the entire vessel is spotless and very modern. There is a huge lounging area at the front of the boat too which is seldom seen. Looking forward to booking with Monika again!
Jahkayah
SUCCESSION: Explore Chicago in Style 32ft Sundancer w/ Captain & Fuel Included!
What a fantastic experience! I rented Alex's boat yesterday and had an absolute blast with my group of 12 friends. From the moment we arrived, Alex was super friendly and welcoming. He showed us around the boat and made sure we felt comfortable and at ease. The boat itself was immaculate - clean, well-maintained, and organized to perfection. Alex had thought of everything to ensure our day on the water was stress-free and enjoyable. His assistant was also super helpful in getting us settled and answering any questions we had. Alex himself was an absolute pleasure to be around. He was knowledgeable about the area and gave us great recommendations for things to do and see. His enthusiasm was infectious, and he really made us feel like we were part of his own little crew. We had an amazing time cruising around the water, taking in the sights, and enjoying each other's company. The boat handled beautifully, and we were able to fit all 12 of us comfortably. Overall, I would highly recommend renting from Alex. His attention to detail, warm hospitality, and love for boating make for a truly unforgettable experience. We can't wait to come back and do it again!
PH
Pat
2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
Natalia was so great to work with! The boat was amazing and we had the best time! Can’t wait to book her boat again.
Jay
2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
Monika and Mario were great! This was our best charter by far.
CC
Chris
Learn Kiteboarding in Chicago, Illinois
Was a great first experience, look forward to taking further lessons. Mike was very knowledgeable and made learning to fly the kite a blast!
EH
Erin
2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
Had the best time. Absolute best boat and best captains we have ever rented in Chicago!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
April 17, 2024
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August 24, 2023
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May 03, 2023
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October 11, 2021
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March 27, 2020
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June 02, 2023
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